S 02 | Ep 5 CEO Lessons from Scaling Meetup , Investopedia & More David Siegel has built and led some of the most recognizable names in digital media , serving as CEO of Meetup and Investopedia and president of Seeking Alpha , guiding each to exits of 5X to 7X . He is also a Columbia professor and author of the bestselling book Decide and Conquer . In this episode , David opens up about his career from early days at DoubleClick , one of New York ' s most influential early internet companies , through his time at IAC and eventually WeWork , where he led Meetup before executing a management buyout of the company . He shares what made Seeking Alpha ' s community so unusually rich , pointing to a contributor network of deeply engaged financial thinkers whose comment sections became a kind of open - source equity research forum . On Meetup , David speaks with genuine conviction about the loneliness epidemic and what happens when people are separated from the community - driven existence humans are wired for . He shares stories of people who found jobs , spouses , and life - changing support groups through in - person gatherings , and makes a case for why authentic connection , both personal and professional , is not a soft priority but a fundamental human need .